  | Jan 1 | 1 | Jan 1 | Thu | Day | MBSA-S | 5,259.5 | 9 | Constitution YC  | Jack Roberts Memorial NYD Race | | HCP | | results | Info | Results |
| | Jan 07 | 2 | Jan 07 | Wed | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing  | Boston - Debrief To Increase Regatta Participation in 2026 | | Soc | | past | Info | RSVP Closed |
| | Jan 11 | 3 | Jan 11 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet  | Sunday Fun | | SS | | results | Info | Results |
| | Jan 14 | 4 | Jan 14 | Wed | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | South Shore - Debrief To Increase Regatta Participation in 2026 | | Soc | | past | Info | RSVP Closed |
| | Jan 15 | 5 | Jan 15 | Thu | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | North Shore - Debrief To Increase Regatta Participation in 2026 | | Soc | | past | Info | RSVP Closed |
| | Jan 17 | 6 | Jan 17 | Sat | Day | GYA | 6,047.9 | 637 | Pensacola Beach YC  | Frostbite Regatta | | HCP | | results | Info | Results |
| | Feb 1 | 7 | Feb 1 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | RDMS 1 | | SS | RDM | results | Info | Results |
| | Feb 03 | 8 | Feb 03 | Tue | Eve | MBSA | 5,259.5 | 9 | Constitution YC | CYC Winter Social | | Soc | | past | Info | RSVP Closed |
| | Feb 8 | 9 | Feb 8 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | RDMS 2 | | SS | RDM | results | Info | Results |
| | Feb 14 | 10 | Feb 14 | Sat | Day | GYA | 6,047.9 | 637 | Pensacola Beach YC | Valentines Regatta | | HCP | | past | Info | Results |
| | Feb 18 | 11 | Feb 18 | Wed | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | Snowflake Regatta Warm-Up Social | | Soc | | past | Info | RSVP Closed |
| | Feb 21,22 | 12 | Feb 21,22 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC  | Harken #1 Optimist Spring Regatta Championship Fleet | | Jr | | results | Info | Results |
| | Feb 21,22 | 13 | Feb 21,22 | Sat,Sun | Day | SCYA | 7,825.4 | 172 | California YC | Harken #1 Optimist Spring Regatta Green Fleet | | Jr | | results | Info | Results |
| | Feb 25 | 14 | Feb 25 | Wed | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | Harbor Hacks: Tides & Tactics- Boston Harbor | | Soc | | past | Info | RSVP Closed |
| | Feb 28... | 15 | Feb 28,Mar 1 | Sat,Sun | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | SCYA MidWinters | | OD | | results | Info | Results |
| | Feb 28... | 16 | Feb 28,Mar 28,Apr 19,May 16,30 | Sat,... | Day | GYA | 6,224.9 | 484 | Southern YC  | HC Spring Race Days | | HCP | OS, CS | results | Info | Results |
| | Feb 28 | 17 | Feb 28 | Sat | Day | GYA | 6,055.3 | 644 | Navy YC Pensacola  | Maxine #1 CC#1 | | HCP | | results | Info | Results |
| | Mar 04 | 18 | Mar 04 | Wed | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | Harbor Hacks: Tides & Tactics- Hingham Bay | | Soc | | past | Info | RSVP Closed |
| | Mar 05 | 19 | Mar 05 | Thu | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | Harbor Hacks: Tides & Tactics- Marblehead | | Soc | | past | Info | RSVP Closed |
| | Mar 7 | 20 | Mar 7 | Sat | Day | GYA | 6,047.9 | 637 | Pensacola Beach YC | Maxine #2 Regatta | | HCP | | past | Info | Results |
| | Mar 8 | 21 | Mar 8 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | Sunday Fun | | SS | | results | Info | Results |
| | Mar 14 | 22 | Mar 14 | Sat | Day | GYA | 6,053.6 | 515 | Pensacola YC  | Maxine #3 | | HCP | | results | Info | Results |
| | Mar 14 | 23 | Mar 14 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC  | Spinnaker Series Race #1 - The Stoney Special* | Y | HCP | | results | Info | Results |
| | Mar 25 | 24 | Mar 25 | Wed | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | CYC & MBSA Rules Refresher- Boston | | Soc | | past | Info | RSVP Closed |
| | Mar 29 | 25 | Mar 29 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | RDMS 3 | | HCP | RDM | results | Info | Results |
| | Apr 01 | 26 | Apr 01 | Wed | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | MBSA Rules Refresher- South Shore | | Soc | | past | Info | RSVP Closed |
| | Apr 02 | 27 | Apr 02 | Thu | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | MBSA Rules Refresher- North Shore | | Soc | | past | Info | RSVP Closed |
| | Apr 11 | 28 | Apr 11 | Sat | Day | GYA | 6,055.3 | 644 | Navy YC Pensacola | 2026 NYCP Bikini Regatta | | HCP | | results | Info | Results |
| | Apr 12 | 29 | Apr 12 | Sun | Day | GYA | 6,047.9 | 637 | Pensacola Beach YC | Race for the Roses | | HCP | | results | Info | Results |
| | Apr 12 | 30 | Apr 12 | Sun | Day | | 7,825.4 | 172 | California YC | Harris Spring Regatta | | HCP | | results | Info | Results |
| | Apr 15... | 31 | Apr 15,22,29,May 6,13,20,27,Jun 3,10,17,24,Jul 1,8,15,22,29,Aug 5,12,19,26,Sep 2 | Wed | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | Sunset Series | | HCP | | regopen | Info | Register |
| | Apr 15 | 32 | Apr 15 | Wed | Eve | MBSA | 5,259.5 | 9 | Constitution YC | Shorthanded Shortcuts | | Soc | | past | Info | RSVP Closed |
| | Apr 16... | 33 | Apr 16,23,30,May 7,14,21,28,Jun 4,11,18 | Thu | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Twilights First Half | Y | HCP | | results | Info | Results |
| | Apr 18 | 34 | Apr 18 | Sat | Day | | 6,071.1 | 645 | Point YC  | Fast Women Regatta 2026 | | HCP | | results | Info | Results |
| | Apr 25 | 35 | Apr 25 | Sat | Day | GYA | 6,055.3 | 644 | Navy YC Pensacola | C C #2 | | HCP | | results | Info | Results |
| | Apr 25,25 | 36 | Apr 25,25 | Sat | Day | GYA | 6,103.4 | 370 | Buccaneer YC  | 66th Dauphin Island Race | | HCP | | results | Info | Results |
| | Apr 26 | 37 | Apr 26 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | Sunday fun April 26 | | SS | | results | Info | Results |
| | Apr 30 | 38 | Apr 30 | Thu | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | Wicked Smaaht Sailah Skillz: Team Building & Social!! (North Shore) | | Soc | | past | Info | RSVP Closed |
| | May 2 | 39 | May 2 | Sat | Day | GYA | 6,053.6 | 515 | Pensacola YC | Fiesta Pensacola / Cancer Society | | HCP | | past | Info | Reg Closed |
| | May 3 | 40 | May 3 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | Sunday fun may 3 | | SS | | results | Info | Results |
| | May 6,... | 41 | May 6,13,20,27,Jun 3,10 | Wed | Day | CBYRA-SoMD | 5,468.9 | 633 | Cambridge YC  | Choptank Series 1 | | HCP | | results | | Results |
| | May 06 | 42 | May 06 | Wed | Eve | MBSA | 5,251.4 | 2 | Hingham Bay Racing  | 2026 Spring Meeting & 2025 Season Awards | | Soc | | past | Info | RSVP Closed |
| | May 6 | 43 | May 6 | Wed | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Regata al Sol | | HCP | | results | Info | Results |
| | May 7 | 44 | May 7 | Thu | Day | | 5,240.3 | 146 | SailMaine  | SailMaine Crew Match Party | | HCP | | past | Info | |
| | May 9 | 45 | May 9 | Sat | Day | GYA | 6,224.9 | 484 | Southern YC | SYC Masters Regatta | | HCP | | past | Info | Reg Closed |
| | May 9 | 46 | May 9 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #2 - TransHarbor Race* | Y | HCP | | results | Info | Results |
| | May 9 | 47 | May 9 | Sat | Day | | 7,825.6 | 208 | King Harbor YC | THE BUD GARDINER BOWL | | OD | | results | Info | Results |
| | May 10 | 48 | May 10 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | Sunday fun May 10 | | SS | | past | Info | Reg Closed |
| | May 13... | 49 | May 13,20,27,Jun 3,17 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Spring Series - Wednesday Night Racing | | HCP | CUP | results | Info | Results |
| | May 13 | 50 | May 13 | Wed | Eve | MBSA | 5,259.5 | 9 | Constitution YC | 2026 Season Kick Off & Skippers Meeting | | Soc | | past | Info | RSVP Closed |
| | May 14 | 51 | May 14 | Thu | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | Mass Bay Sailing Season Kick Off Party- South | | Soc | | past | Info | RSVP Closed |
| | May 15 | 52 | May 15 | Fri | Eve | MBSA | 5,259.6 | 4 | Mass Bay Sailing | Mass Bay Sailing Season Kick Off Party- North | | Soc | | past | Info | RSVP Closed |
| | May 16 | 53 | May 16 | Sat | Day | SCYA-MDR/RB | 7,825.4 | 721 | Port Royal YC  | Port Royal Classic | | HCP | | results | Info | Results |
| | May 16,17 | 54 | May 16,17 | Sat,Sun | Day | GYA | 6,053.6 | 515 | Pensacola YC | Pensacola Multihull Regatta | | HCP | | results | Info | Results |
| | May 16 | 55 | May 16 | Sat | Day | GYA | 6,047.9 | 637 | Pensacola Beach YC | Sea Buoy Regatta | | HCP | RDM | results | Info | Results |
| | May 20... | 56 | May 20,27,Jun 3,10,17,24,Jul 1,9,15,22,29,Aug 5,12,19,26 | Wed,... | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC  | CYC Wednesday Summer Series | | HCP | | regopen | Info | Register |
| | May 20 | 57 | May 20 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC  | Wednesday Evening Spring Series | | HCP | | past | Info | |
| | May 23 | 58 | May 23 | Sat | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Memorial Day Regatta | | HCP | | past | Info | |
| | May 24 | 59 | May 24 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | Sunday fun may 24 | | SS | | past | Info | Reg Closed |
| | May 25 | 60 | May 25 | Mon | Day | MBSA-N | 5,250.6 | 7 | Eastern YC  | EYC Tour the BAY Pursuit Race | | PUR | | results | Info | Results |
| | May 27... | 61 | May 27,Jun 3,17,24,Jul 1,8 | Wed | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | CPYC/BHHR Wed Night Racing Series 1 | Y | HCP | | results | Info | Results |
| | May 27... | 62 | May 27,Jun 3,10,17,24,Jul 1 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constitution YC | CYC Wednesday Evening Spring Series | Y | HCP | WNR | results | Info | Results |
| | May 28 | 63 | May 28 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46  | Spring Series 1 of 4 | Y | OD | | past | Info | Register |
| | May 30 | 64 | May 30 | Sat | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | Cal Race Week | | HCP | | results | Info | Results |
| | Jun 2,... | 65 | Jun 2,9,16,23 | Tue | Eve | SCYA-MDR/RB | 7,825.4 | 721 | Port Royal YC | June Cup - Women at the Helm | | HCP | | results | Info | Results |
| | Jun 4 | 66 | Jun 4 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Spring Series 2 of 4 (Combined Night 1 of 6) | Y | OD | | results | Info | Register |
| | Jun 4,... | 67 | Jun 4,11,18,25,Jul 9,16,23,Aug 6,13,20,27,Sep 3,10 | Thu | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC  | Thunderbird Twilight Series | | OD | | regopen | Info | Register |
| | Jun 6 | 68 | Jun 6 | Sat | Day | GYA | 6,055.3 | 644 | Navy YC Pensacola | 2026 Navy Cup | | HCP | | results | Info | Results |
| | Jun 6 | 69 | Jun 6 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Centerboard Regatta | | HCP | Ovr | results | Info | Results |
| | Jun 7 | 70 | Jun 7 | Sun | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Circle The Lights | | HCP | BKT | results | Info | Results |
| | Jun 7 | 71 | Jun 7 | Sun | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Spinnaker Series Race #3 - Eagle Rock to MDR | Y | HCP | | results | Info | Results |
| | Jun 07 | 72 | Jun 07 | Sun | Eve | MBSA | 5,257.9 | 154 | Savin Hill YC | Massachusetts Boating Safety Course - US Coast Guard Auxiliary | | Soc | | past | Info | RSVP Closed |
| | Jun 7 | 73 | Jun 7 | Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead  | Somerset Regatta | | HCP | | results | Info | Results |
| | Jun 9,... | 74 | Jun 9,16,30,Jul 7,14,21,28,Aug 4,11,18,25,Sep 1,8 | Tue | Eve | GMORA-P | 5,192.9 | 74 | Rockland YC  | Tuesday Night Series | | HCP | | regopen | Info | Register |
| | Jun 10 | 75 | Jun 10 | Wed | Day | MBSA-S | 5,259.5 | 9 | Constitution YC | Greater Boston Rumble I | | HCP | GBR | results | Info | Results |
| | Jun 11 | 76 | Jun 11 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Spring Series 3 of 4 | Y | OD | | results | Info | Register |
| | Jun 12 | 77 | Jun 12 | Fri | Day | MBSA-N | 5,251.1 | 6 | Boston YC | PHRF New England Championship | | HCP | | past | Info | |
| | Jun 12... | 78 | Jun 12,26,Jul 10,24,Aug 7,21 | Fri | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Savin Hill Friday Handicap Twilight Series Div. 1 | | HCP | | regopen | Info | Register |
| | Jun 12... | 79 | Jun 12,26,Jul 10,24,Aug 7,21 | Fri | Eve | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Savin Hill Friday Handicap Twilight Series Div. 2 | | HCP | | regopen | Info | Register |
| | Jun 13... | 80 | Jun 13,14,27,28 | Sat,... | Day | GMORA-P | 5,192.6 | 79 | Camden YC  | CYC Summer Series | | HCP | Ovr | results | Info | Results |
| | Jun 13 | 81 | Jun 13 | Sat | Day | | 6,053.6 | 515 | Pensacola YC | Two-Bridge Farce Regatta | | HCP | RDM | results | Info | Results |
| | Jun 13 | 82 | Jun 13 | Sat | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Race to the Coast | | SS | | results | Info | Results |
| | Jun 17... | 83 | Jun 17,24,Jul 8,15,22,29 | Wed | Eve | CBYRA-SoMD | 5,468.9 | 633 | Cambridge YC | Choptank Series 2 | | HCP | | regopen | Info | |
| | Jun 18 | 84 | Jun 18 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Spring Series 4 of 4 (Combined Night 2 of 6) | Y | OD | | past | Info | Register |
| | Jun 19 | 85 | Jun 19 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC FRI Pursuit Race #1 | Y | PUR | | results | Info | Results |
| | Jun 19 | 86 | Jun 19 | Fri | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Solstice Regatta | | HCP | BKT | results | Info | Results |
| | Jun 20 | 87 | Jun 20 | Sat | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | R19 Saturday June Regatta | Y | OD | | results | Info | Register |
| | Jun 20 | 88 | Jun 20 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Solstice Race | | HCP | Ovr | results | Info | Results |
| | Jun 20 | 89 | Jun 20 | Sat | Day | MBSA-S | 5,259.5 | 9 | Constitution YC | Constitution Yacht Club & Savin Hill Yacht Club Memorial Regatta | | HCP | | results | Info | Results |
| | Jun 20 | 90 | Jun 20 | Sat | Day | GMORA-W | 5,236.3 | 73 | Harraseeket YC  | Harraseeket Regatta | | PUR | Ovr | results | Info | Results |
| | Jun 21 | 91 | Jun 21 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC  | MYC Patton Bowl | | HCP | | results | Info | Results |
| | Jun 21 | 92 | Jun 21 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | RDMS 6 | | SS | RDM | results | Info | Results |
| | Jun 24... | 93 | Jun 24,Jul 1,8,22,29 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Summer Series - Wednesday Night Racing | | HCP | CUP | regopen | Info | Register |
| | Jun 24 | 94 | Jun 24 | Wed | Day | MBSA-S | 5,259.5 | 9 | Constitution YC | Humpday Harbor Hustle Series Race 1 | | HCP | | results | Info | Results |
| | Jun 25... | 95 | Jun 25,Jul 2,9,16,30,Aug 6,13,20,27,Sep 3,10 | Thu | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Twilights Second Half | Y | HCP | | regopen | Info | Register |
| | Jun 25 | 96 | Jun 25 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Summer Series 1 of 5 | Y | OD | | results | Info | Register |
| | Jun 26 | 97 | Jun 26 | Fri | OvrNt | GYA | 6,224.9 | 484 | Southern YC | Gulfport to Pensacola Race | | HCP | | past | Info | Results |
| | Jun 26 | 98 | Jun 26 | Fri | OvrNt | MBSA-N | 5,250.6 | 7 | Eastern YC | Lambert Overnight Ocean Race | | HCP | | results | Info | Results |
| | Jun 27 | 99 | Jun 27 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Constitution Cup - a MBSA Qualifier | | HCP | | past | Cancelled | Reg Closed |
| | Jun 28... | 100 | Jun 28,Jul 5,12,19,26,Aug 1,9 | Sun,... | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club  | Northport Yacht Club Rhodes 19 Series | | OD | | regopen | Info | Register |
| | Jun 28... | 101 | Jun 28,Jul 5,12,19,26,Aug 1,9 | Sun,... | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | JOHN SHORT RACE PHRF | | HCP | | regopen | Info | Register |
| | Jun 28 | 102 | Jun 28 | Sun | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | FAST MERMAID - Charity Race | | PUR | | past | Info | Results |
| | Jun 30 | 103 | Jun 30 | Tue | Day | MBSA-N | 5,248.6 | 101 | Manchester Sailing  | Manchester Green Regatta | | Jr | | results | Info | Results |
| | Jul 1 | 104 | Jul 1 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC | Wednesday Evening Summer Series | | HCP | | past | Info | |
| | Jul 2 | 105 | Jul 2 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Summer Series 2 of 5 (Combined Night 3 of 6) | Y | OD | | results | Info | Register |
| | Jul 4 | 106 | Jul 4 | Sat | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Annual Regatta - 156th Anniversary | | HCP | | results | Info | Results |
| | Jul 5 | 107 | Jul 5 | Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC  | BHYC Classics Race | | PUR | Ovr | results | Info | Results |
| | Jul 8,... | 108 | Jul 8,15,22,29,Aug 5,12 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constitution YC | CYC Wednesday Evening Summer Series | Y | HCP | WNR | regopen | Info | Register |
| | Jul 8,9 | 109 | Jul 8,9 | Wed,Thu | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | Battle of the Bay Junior Regatta | | Jr | | results | Info | Results |
| | Jul 9 | 110 | Jul 9 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Summer Series 3 of 5 | Y | OD | | results | Info | Register |
| | Jul 10... | 111 | Jul 10,11,12 | Fri,... | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | M242 North American Championship | | OD | | results | Info | Results |
| | Jul 10 | 112 | Jul 10 | Fri | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC  | JYC Short-handed Regatta | | HCP | | results | Info | Results |
| | Jul 10 | 113 | Jul 10 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC FRI Pursuit Race #2 | Y | PUR | | results | Info | Results |
| | Jul 11 | 114 | Jul 11 | Sat | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | S.S. Crocker Memorial Race | | PUR | | results | Info | Results |
| | Jul 11 | 115 | Jul 11 | Sat | Eve | MBSA | 5,259.5 | 9 | Constitution YC | Boston Tall Ships Harbor Island Flotilla July | | Soc | | past | Info | RSVP Closed |
| | Jul 11,12 | 116 | Jul 11,12 | Sat,Sun | Day | GMORA-W | 5,239.6 | 71 | Portland YC  | The Pilot Regatta | | HCP | Ovr | results | Info | Results |
| | Jul 11,12 | 117 | Jul 11,12 | Sat,Sun | Day | SCYA-MDR/RB | 7,825.4 | 172 | California YC | King of Spain | | OD | | results | Info | Results |
| | Jul 11,12 | 118 | Jul 11,12 | Sat,Sun | Day | GMORA-P | 5,192.6 | 79 | Camden YC | King of Spain Series | | PUR | | results | Info | Results |
| | Jul 12 | 119 | Jul 12 | Sun | Day | MBSA | 5,250.4 | 3 | Corinthian Marblehead | Midsummer Ocean Race (Pursuit) | | PUR | | results | Info | Results |
| | Jul 12 | 120 | Jul 12 | Sun | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Boston Harbor Ladies Challenge | | HCP | | results | Info | Results |
| | Jul 15 | 121 | Jul 15 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Greater Boston Rumble II | | HCP | GBR | past | Info | Reg Closed |
| | Jul 15,16 | 122 | Jul 15,16 | Wed,Thu | Day | GMORA-W | 5,236.3 | 73 | Harraseeket YC | HYC Youth Regatta | | Jr | | past | Info | Reg Closed |
| | Jul 16 | 123 | Jul 16 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Summer Series 4 of 5 (Combined Night 4 of 6) | Y | OD | | past | Info | Register |
| | Jul 17 | 124 | Jul 17 | Fri | OvrNt | MBSA-N | 5,251.1 | 6 | Boston YC | Beringer Bowl Overnight Ocean Race | | HCP | | past | Info | |
| | Jul 18,19 | 125 | Jul 18,19 | Sat,Sun | Day | GMORA-B | 5,214.3 | 78 | Boothbay Harbor YC | BHYC Regatta & Shipyard Cup Classics Challenge | | HCP | Ovr | past | Info | Reg Closed |
| | Jul 18 | 126 | Jul 18 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Race to the Graves | | PUR | Ovr | past | Info | Reg Closed |
| | Jul 19 | 127 | Jul 19 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | RDMS 7 | | HCP | RDM | past | Info | Reg Closed |
| | Jul 22... | 128 | Jul 22,29,Aug 12,19,26,Sep 2,9 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | BHHR/CPYC Wed Night Racing Series II | Y | HCP | | regopen | Info | Register |
| | Jul 23,25 | 129 | Jul 23,25 | Thu,Sat | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Thunderbird Spirit Series | | OD | | regopen | Info | Register |
| | Jul 23 | 130 | Jul 23 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Summer Series 5 of 5 | Y | OD | | regopen | Info | Register |
| | Jul 24 | 131 | Jul 24 | Fri | OvrNt | MBSA-N | 5,251.2 | 44 | Marblehead YC  | Downeast Challenge | | HCP | Ovr | regopen | Info | Register |
| | Jul 24,25 | 132 | Jul 24,25 | Fri,Sat | Day | GMORA-P | 5,192.7 | 80 | Camden Classics Cup  | Camden Classics Cup | | HCP | Ovr | regopen | Info | Reg Closed |
| | Jul 25,26 | 133 | Jul 25,26 | Sat,Sun | Day | MBSA-S | 5,255.8 | 51 | Squantum YC  | Lipton Cup Regatta Juniors | | Jr | | regopen | Info | Register |
| | Jul 26 | 134 | Jul 26 | Sun | Day | GMORA-P | 5,194.4 | 777 | Rockport BC | Paper Cup Challenge | | PUR | Ovr | regopen | Info | Register |
| | Jul 30... | 135 | Jul 30,31,Aug 1,2 | Thu,... | Day | | 5,257.9 | 154 | Savin Hill YC | Thunderbird Class Championships | | OD | | regopen | Info | Register |
| | Jul 30 | 136 | Jul 30 | Thu | Day | GMORA-P | 5,183.2 | 138 | Castine YC  | Castine Classic Yacht Race | | HCP | | regopen | Info | Register |
| | Jul 30 | 137 | Jul 30 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Late Summer Series 1 of 5 (Combined Night 5 of 6) | Y | OD | | regopen | Info | Register |
| | Jul 31 | 138 | Jul 31 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC FRI Pursuit Race #3 | Y | PUR | | regopen | Info | Register |
| | Jul 31 | 139 | Jul 31 | Fri | Day | GMORA-P | 5,192.6 | 79 | Camden YC | CYC Classic Yacht Feeder Race | | HCP | | regopen | Info | Register |
| | Jul 31 | 140 | Jul 31 | Fri | OvrNt | GMORA-W | 5,239.6 | 71 | Portland YC | Monhegan Island Race & Seguin Sprint | | HCP | Ovr | regopen | Info | Reg Closed |
| | Aug 1 | 141 | Aug 1 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC  | Cape Ann Challenge | | HCP | | regopen | Info | Register |
| | Aug 1 | 142 | Aug 1 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Phil Small Regatta | | PUR | | regopen | Info | Register |
| | Aug 1 | 143 | Aug 1 | Sat | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | 32nd CPYC Pursuit Race to Benefit Make-A-Wish | | PUR | | regopen | Info | Register |
| | Aug 1,2 | 144 | Aug 1,2 | Sat,Sun | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC  | CPYC RegattaTo Benefit Make-A-Wish One Design/ Snipe New England's | | OD | | regopen | Info | Register |
| | Aug 1,2 | 145 | Aug 1,2 | Sat,Sun | Day | MBSA-S | 5,255.8 | 11 | Cottage Park YC | CPYC Youth Regatta to Benefit Make A Wish | | Jr | | regopen | Info | Register |
| | Aug 1,2 | 146 | Aug 1,2 | Sat,Sun | Day | SCYA | 7,825.7 | 253 | Womens Sailing Association (SMB)  | WOW/WAH | | HCP | | regopen | Info | Register |
| | Aug 2 | 147 | Aug 2 | Sun | Day | MBSA-N | 5,253.2 | 30 | Palmers Cove YC  | Mass Bay Shorthanded Regatta | | HCP | | regopen | Info | Register |
| | Aug 5 | 148 | Aug 5 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | Greater Boston Rumble III | | HCP | GBR | regopen | Info | Reg Closed |
| | Aug 6 | 149 | Aug 6 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Late Summer Series 2 of 5 | Y | OD | | regopen | Info | Register |
| | Aug 7 | 150 | Aug 7 | Fri | Day | MBSA-S | 5,259.5 | 9 | Constitution YC | Harbor Hop | | HCP | | regopen | Info | Register |
| | Aug 8,9 | 151 | Aug 8,9 | Sat,Sun | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Corinthian Classic Yacht Regatta | | PUR | | future | Info | Reg Not Open |
| | Aug 8 | 152 | Aug 8 | Sat | Day | GMORA-W | 5,240.3 | 146 | SailMaine | SailMaine Festival and Regatta | | HCP | Ovr | regopen | Info | Register |
| | Aug 8 | 153 | Aug 8 | Sat | Day | MBSA-S | 5,259.1 | 41 | Courageous SC  | Flip Flop Regatta | | PUR | | regopen | Info | Register |
| | Aug 8 | 154 | Aug 8 | Sat | Day | SCYA-MDR/RB | 7,825.6 | 208 | King Harbor YC | Queen Mary Regatta | | HCP | | regopen | Info | Register |
| | Aug 9 | 155 | Aug 9 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | RDMS 8 | | SS | RDM | regopen | Info | Register |
| | Aug 09 | 156 | Aug 09 | Sun | Eve | MBSA | 5,259.5 | 9 | Constitution YC | Boston Harbor Island Flotilla August | | Soc | | regopen | Info | RSVP |
| | Aug 12 | 157 | Aug 12 | Wed | Eve | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | CPYC/BHHR and CYC Humpday Hustle | | HCP | | regopen | Info | Register |
| | Aug 12 | 158 | Aug 12 | Wed | Eve | MBSA-N | 5,251.1 | 6 | Boston YC | Wednesday Evening Fall Series | | HCP | | regopen | Info | |
| | Aug 12... | 159 | Aug 12,19,26,Sep 2,9 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Fall Series - Wednesday Night Racing | | HCP | CUP | regopen | Info | Register |
| | Aug 13 | 160 | Aug 13 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Late Summer Series 3 of 5 (Combined Night 6 of 6) | Y | OD | | regopen | Info | Register |
| | Aug 14 | 161 | Aug 14 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC FRI Pursuit Race #4 | Y | PUR | | regopen | Info | Register |
| | Aug 15 | 162 | Aug 15 | Sat | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Rhodes to Glory | Y | OD | | regopen | Info | Register |
| | Aug 15 | 163 | Aug 15 | Sat | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Centerboard Yacht Club Bluewater Regatta | | HCP | Ovr | regopen | Info | Register |
| | Aug 15 | 164 | Aug 15 | Sat | Day | GMORA-P | 5,183.4 | 315 | Maine Maritime Academy | Maine Retired Skippers Race | | PUR | | regopen | Info | Register |
| | Aug 15 | 165 | Aug 15 | Sat | Day | SCYA-MDR/RB | 7,825.4 | 721 | Port Royal YC | Pirate Regatta - High Point Race #8 | | HCP | | regopen | Info | Register |
| | Aug 15 | 166 | Aug 15 | Sat | Day | GMORA-P | 5,192.9 | 74 | Rockland YC | Scholarship Race | | HCP | Ovr | regopen | Info | Register |
| | Aug 19... | 167 | Aug 19,26,Sep 2,9,16,23 | Wed | Eve | MBSA-S | 5,259.5 | 9 | Constitution YC | CYC Wednesday Evening Fall Series | Y | HCP | WNR | regopen | Info | Register |
| | Aug 20 | 168 | Aug 20 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Not Going to Nationals - R19 Thursday Night Racing (Spinnaker Optional) | Y | OD | | regopen | Info | Register |
| | Aug 21 | 169 | Aug 21 | Fri | Eve | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC FRI Pursuit Race #5 | Y | PUR | | regopen | Info | Register |
| | Aug 22 | 170 | Aug 22 | Sat | Eve | SCYA | 7,825.4 | 172 | California YC | Sanguinetti | | Soc | | regopen | Info | RSVP |
| | Aug 22 | 171 | Aug 22 | Sat | Day | MBSA-S | 5,249.5 | 26 | Hingham YC  | Ethan W. Hitchcock Trophy Race | | HCP | BKT | regopen | Info | Register |
| | Aug 22 | 172 | Aug 22 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Round the Salvages Pursuit Race | | PUR | | regopen | Info | Register |
| | Aug 22,23 | 173 | Aug 22,23 | Sat,Sun | Day | GMORA-W | 5,240.0 | 72 | Centerboard YC | Quahog Quest | | HCP | Ovr | regopen | Info | Register |
| | Aug 23 | 174 | Aug 23 | Sun | Day | MBSA-N | 5,251.2 | 44 | Marblehead YC | Clemson Chase Race | | PUR | | regopen | Info | Register |
| | Aug 23 | 175 | Aug 23 | Sun | Day | NJYRA | 5,404.5 | 869 | Rutgers Sailing  | Rutgers Raritan Rah-Rah-Regatta | | OD | | regopen | Info | Register |
| | Aug 23 | 176 | Aug 23 | Sun | Day | MBSA-S | 5,255.9 | 12 | Boston Harbor Handicap Racing | 40th Annual JFK Regatta - A Mass Bay Qualifier | | HCP | | regopen | Info | Register |
| | Aug 27 | 177 | Aug 27 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Late Summer Series 4 of 5 | Y | OD | | regopen | Info | Register |
| | Aug 29 | 178 | Aug 29 | Sat | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Hosea White Race | | HCP | | regopen | Info | Register |
| | Aug 30 | 179 | Aug 30 | Sun | Day | MBSA-N | 5,251.1 | 6 | Boston YC | James R. Hodder Ocean Race | | HCP | | future | Info | |
| | Aug 30 | 180 | Aug 30 | Sun | Day | GMORA-P | 5,192.6 | 79 | Camden YC | Camden Yacht Club Solo Challange | | PUR | Ovr | regopen | Info | Register |
| | Sep 2,... | 181 | Sep 2,9,16,23,30 | Wed | Eve | GMORA-W | 5,240.0 | 72 | Centerboard YC | CYC Wednesday Fall Series | | HCP | | regopen | Info | Register |
| | Sep 3 | 182 | Sep 3 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Late Summer Series 5 of 5 | Y | OD | | regopen | Info | Register |
| | Sep 5 | 183 | Sep 5 | Sat | Day | MBSA-N | 5,243.2 | 14 | Eastern Point YC | Bobby Veltman Memorial Pursuit Race | | PUR | | regopen | Info | Register |
| | Sep 7 | 184 | Sep 7 | Mon | Day | MBSA-N | 5,251.1 | 6 | Boston YC | Sail Salem Pursuit Race | | PUR | | future | Info | |
| | Sep 10 | 185 | Sep 10 | Thu | Eve | MBSA-S | 5,250.3 | 18 | Rhodes 19 Fleet 46 | Grab and Drink and Go! | Y | OD | | regopen | Info | Register |
| | Sep 12 | 186 | Sep 12 | Sat | Day | GMORA-P | 5,193.9 | 143 | Northport Yacht Club | AROUND ISLESBORO RACE | | HCP | Ovr | regopen | Info | Register |
| | Sep 12 | 187 | Sep 12 | Sat | Day | GYA | 6,047.9 | 637 | Pensacola Beach YC | Big Mouth Regatta | | HCP | RDM | regopen | Info | Register |
| | Sep 12 | 188 | Sep 12 | Sat | OvrNt | GMORA-P | 5,192.9 | 74 | Rockland YC | Maine Rocks | | HCP | Ovr | regopen | Info | Register |
| | Sep 12 | 189 | Sep 12 | Sat | Day | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Chowder Cup | | HCP | BKT | regopen | Info | Register |
| | Sep 12 | 190 | Sep 12 | Sat | Eve | SCYA | 7,825.4 | 172 | California YC | Cal YC 2x2 Invitational Team Race | | Soc | | regopen | Info | RSVP |
| | Sep 12 | 191 | Sep 12 | Sat | Day | MBSA-N | 5,253.2 | 8 | Jubilee YC | Jubilee Annual Regatta | | HCP | | regopen | Info | Register |
| | Sep 13 | 192 | Sep 13 | Sun | Day | | 5,404.5 | 869 | Rutgers Sailing | Rutgers Alumni Regatta | | OD | | regopen | Info | Register |
| | Sep 13 | 193 | Sep 13 | Sun | Day | MBSA-N | 5,248.6 | 29 | Manchester YC | Manchester Fall Series | | HCP | | regopen | Info | Register |
| | Sep 16... | 194 | Sep 16,23,30 | Wed | Eve | MBSA-S | 5,251.4 | 2 | Hingham Bay Racing | Hall Pass Series - Wednesday Night Racing | | HCP | | regopen | Info | Register |
| | Sep 19 | 195 | Sep 19 | Sat | Day | MBSA-S | 5,250.2 | 1 | Hull YC  | HYC Great Chase Race | | PUR | | regopen | Info | Register |
| | Sep 19 | 196 | Sep 19 | Sat | Day | GYA | 6,055.3 | 644 | Navy YC Pensacola | 2026 Beverly Stagg Regatta CC#3 | | HCP | | regopen | Info | Register |
| | Sep 20 | 197 | Sep 20 | Sun | Day | MBSA | 5,250.6 | 7 | Eastern YC | Marblehead Chowder Cup | | HCP | | regopen | Info | Register |
| | Sep 20... | 198 | Sep 20,Oct 3,18,Nov 14,Dec 5 | Sun,... | Day | GYA | 6,224.9 | 484 | Southern YC | HC Fall Race Days | | HCP | | regopen | Info | Register |
| | Sep 24... | 199 | Sep 24,25,26 | Thu,... | Day | | 6,047.9 | 637 | Pensacola Beach YC | Pensacola Beach Multihull Race & Cruise Week | | HCP | | regopen | Info | Register |
| | Sep 26 | 200 | Sep 26 | Sat | Day | MBSA-S | 5,257.9 | 154 | Savin Hill YC | Boston Light Race | | PUR | | regopen | Info | Register |
| | Sep 26 | 201 | Sep 26 | Sat | Day | GYA | 6,055.3 | 644 | Navy YC Pensacola | 2026 Whit Johnson CC#4 | | HCP | | regopen | Info | Register |
| | Sep 27 | 202 | Sep 27 | Sun | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | EYC Pot Luck Pursuit Race | | PUR | | regopen | Info | Register |
| | Oct 3 | 203 | Oct 3 | Sat | Day | MBSA-N | 5,250.4 | 3 | Corinthian Marblehead | Bandit Race - Short Handed | | HCP | | regopen | Info | Register |
| | Oct 3 | 204 | Oct 3 | Sat | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | PUMPKIN PURSUIT RACE SERIES #1 | Y | PUR | | regopen | Info | Register |
| | Oct 17 | 205 | Oct 17 | Sat | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | PUMPKIN PURSUIT RACE SERIES #2 | Y | PUR | | regopen | Info | Register |
| | Oct 24 | 206 | Oct 24 | Sat | Eve | MBSA | 5,259.5 | 9 | Constitution YC | Constitution Yacht Club Annual Meeting & Awards Brunch | | Soc | | regopen | Info | RSVP |
| | Oct 24 | 207 | Oct 24 | Sat | Day | MBSA-N | 5,250.6 | 7 | Eastern YC | PUMPKIN PURSUIT RACE SERIES #3 | Y | PUR | | regopen | Info | Register |
| | Nov 15 | 208 | Nov 15 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | RDMS 11 | | SS | | regopen | Info | Register |
| | Dec 6 | 209 | Dec 6 | Sun | Day | GYA | 6,052.2 | 791 | Pensacola Bay Cruising Fleet | RDMS 12 | | HCP | RDM | regopen | Info | Register |
Regatta Management Solutions (test)